Triethylamine → N-[(3'-bromo-4'-methoxy-1,1'-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide

HRID 493488Notes

Reaction equation

HRID 493488 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](Cl)=[O:12])=[CH:3]1.[Br:14][C:15]1[CH:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH:30][CH3:31])=[CH:25][CH:24]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C(N(CC)CC)C>C(Cl)Cl>[Br:14][C:15]1[CH:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]([CH3:31])[C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[O:12])=[CH:25][CH:24]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151324411-Methyl-1H-indole-3-carbonyl chlorideHCID 68862675N-[(3'-bromo-4'-methoxy-1,1'-biphenyl-4-yl)methyl]-N-methylamine

Product 1

HCID 68860765N-[(3'-bromo-4'-methoxy-1,1'-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-methyl-1H-indole-3-carbonyl chloride (16.3 mmol), prepared in the previous step, in 50 mL of methylene chloride was added under nitrogen dropwise to a solution of N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-N-methylamine (5.00 g, 16.3 mmol), prepared in step 5 of Example 6, and triethylamine (2.3 mL, 16.3 mmol) in 200 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature for 20 h. The reaction was extracted with 1 N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide (7.4 g, 98%) as a white solid foam, MS (ESI) m/z 463 [M+H]+. Elemental Analysis for C25H23BrN2O2. Calc'd: C, 64.80; H, 5.00; N, 6.05 Found: C, 62.88; H, 4.92; N, 5.61

Workup

  1. additionAfter the addition the reaction
  2. extractionThe reaction was extracted with 1 N HCl
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-afd92b478a404338be5fddacd50bcdea
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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